e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Folate antagonists. 20. Synthesis and antitumor and antimalarial properties of trimetrexate and related 6-[(phenylamino) methyl]-2, 4-quinazolinediamines

EF Elslager, JL Johnson, LM Werbel

Index: Elslager, Edward F.; Johnson, Judith L.; Werbel, Leslie M. Journal of Medicinal Chemistry, 1983 , vol. 26, # 12 p. 1753 - 1760

Full Text: HTML

Citation Number: 81

Abstract

A series of 6-[(arylamino) methyl]-2, 4-quinazolinediamines have been prepared by catalytic hydrogenation of the requisite 2, 4-diamino-6-quinazolinecarbonitriles in the presence of the appropriate benzenamine. Formylation, acetylation, and nitrosation provided N" derivatives of these compounds. A variety of the compounds exhibited potent antimalarial, antibacterial, and antitumor activity. In particular, 5-methyl-6-[[(3, 4, 5-trimethoxyphenyl)-amino] methyl]- ...

2-Naphthalenamine,6-chloro- Structure

2-Naphthalenami...

acetic acid Structure

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~34%

acetic acid; 6-[[(6-chloronaphthalen-2-yl)amino]methyl]quinazoline-2,4-diamine Structure

acetic acid; 6-...

2-Naphthalenamine,6-chloro- Structure

2-Naphthalenami...

~%

N-(6-chloronaphthalen-2-yl)-N-[(2,4-diaminoquinazolin-6-yl)methyl]formamide Structure

N-(6-chloronaph...

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~%

N-(6-chloronaphthalen-2-yl)-N-[(2,4-diaminoquinazolin-6-yl)methyl]formamide Structure

N-(6-chloronaph...

Formic Acid Structure

acetic acid; 6-[[(6-chloronaphthalen-2-yl)amino]methyl]quinazoline-2,4-diamine Structure

acetic acid; 6-...

~68%

N-(6-chloronaphthalen-2-yl)-N-[(2,4-diaminoquinazolin-6-yl)methyl]formamide Structure

N-(6-chloronaph...

1-Naphthalenamine,4-chloro- Structure

1-Naphthalenami...

acetic acid Structure

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~26%

2,4-Quinazolinediamine, 6-[[(4-chloro-1-naphthalenyl)amino]methyl]-, acetate (2:3) Structure

2,4-Quinazoline...

acetic acid Structure

3,5-Dichloroaniline Structure

3,5-Dichloroaniline

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~50%

acetic acid,6-[(3,5-dichloroanilino)methyl]quinazoline-2,4-diamine Structure

acetic acid,6-[...

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~%

N-[(2,4-diaminoquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)acetamide Structure

N-[(2,4-diamino...

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~%

N-[(2,4-diaminoquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)acetamide Structure

N-[(2,4-diamino...

Ethanoic anhydride Structure

Ethanoic anhydride

acetic acid; 6-[[(3,4-dichlorophenyl)amino]methyl]quinazoline-2,4-diamine Structure

acetic acid; 6-...

~66%

N-[(2,4-diaminoquinazolin-6-yl)methyl]-N-(3,4-dichlorophenyl)acetamide Structure

N-[(2,4-diamino...

acetic acid Structure

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

2,4-diaminoquinazoline-6-carbonitrile Structure

2,4-diaminoquin...

~58%

acetic acid; 6-[[(3,4-dichlorophenyl)amino]methyl]quinazoline-2,4-diamine Structure

acetic acid; 6-...

6-(((3,4-dichlorophenyl)amino)methyl)-5-methyl-2,4-quiazolinediamine acetate Structure

6-(((3,4-dichlo...

~31%

2,4-Quinazolinediamine,6-[[(3,4-dichlorophenyl)nitrosoamino]methyl]-5-methyl- Structure

2,4-Quinazoline...

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~%

2,4-Quinazolinediamine,6-[[(3,4-dichlorophenyl)nitrosoamino]methyl]-5-methyl- Structure

2,4-Quinazoline...

2,4-Diamino-5-methyl-6-quinazolinecarbonitrile Structure

2,4-Diamino-5-m...

~%

2,4-Quinazolinediamine,6-[[(3,4-dichlorophenyl)nitrosoamino]methyl]-5-methyl- Structure

2,4-Quinazoline...

acetic acid Structure

3-Bromoaniline Structure

2,4-diamino-5-chloroquinazoline-6-carbonitrile Structure

2,4-diamino-5-c...

~15%

acetic acid; 6-[[(3-bromophenyl)amino]methyl]-5-chloro-quinazoline-2,4-diamine Structure

acetic acid; 6-...